The Thanksgiving I Never Expected to Feel Lost

A real story that changed how I see human nature — and the fragility of a life.

01｜A 33-year-old man… still carrying a wound from when he was 19

The story starts with a man who’s 33.

But emotionally, he’s been frozen at 19 —

the year he lost both parents.

From the outside, he looks steady, controlled, adult.

But on the inside, part of him never made it past that week.

I’ve seen this before — especially in finance.

A single tragedy can freeze someone’s emotional growth.

The body ages.

The résumé advances.

But the inner world stays stuck at the break.

And life keeps moving… while they don’t.

02｜His first message wasn’t about money — it was about trust

One day he texted me:

“My lawyer says we should push for 1M.

The other side only wants to give 500k.

I don’t know which to take. Can you help me?”

He wasn’t asking about numbers.

He was asking:

“Who do I believe?

Who’s actually on my side?”

I paused my work, read every document, every clause, every precedent.

Not because the settlement was complicated —

but because his sense of safety depended on clarity.

After reviewing everything, I told him:

“1M is within a fair range.

And remember — your lawyer earns more when you earn more.

They already know how far the other side can go.”

I wasn’t choosing for him.

I was giving him structure —

something he hasn’t had since he was 19.

For the first time in a long time,

he exhaled.

03｜Right before the verdict, I only said three words

On the morning of the hearing, he messaged me.

I could feel the fear behind the words.

I only replied with three:

“Stay steady.”

Not to comfort him —

but to ground him in reality.

A few hours later, he walked out of the courtroom and said:

“950k. Picking up the check on Thursday.”

I felt relieved —

but also very clear-eyed.

So I told him:

“Split it in three.

Three banks.

Three-month cooling period.

We’ll plan after.”

Not because I wanted control.

But because I know this truth:

Money amplifies every fracture inside a person.

Without structure, it becomes a weapon — against themselves.

For the first time in his life,

someone wasn’t teaching him how to earn…

but how to hold money.

04｜But right when the dust settled, the “unhealed parts” surfaced

After the settlement, something shifted.

More messages.

Clingier tone.

He wanted to meet.

To start a business together.

To build a new life — with me in it.

But I’ve seen this pattern too many times:

This wasn’t affection.

It was projection, dependency, emotional gravity —

a child grabbing the nearest sense of safety.

So I told him gently:

“You don’t like me.

You’re holding onto the one steady thing in your life.

You need time — not me.”

No judgment.

Just clarity.

When a person suddenly steps into wealth,

their logic is the first thing to disappear.

What he needed wasn’t Jenna the person —

but Jenna the structure.

05｜And then Thanksgiving arrived — with an unexpected silence

On Thanksgiving, I thought I’d get at least one message.

Something simple.

A thank-you.

A sign of grounding.

But nothing came.

The silence wasn’t painful —

it was revealing.

I realized I forgot something essential:

I’m human too.

Later I told a friend.

She said something that hit me like a clean cut:

“You’re not seeing malice.

You’re seeing his wound.”

And suddenly it all made sense.

What felt like trust, responsibility, connection

was, to him:

dependency, fear, projection,

and the urge to anchor himself to someone stronger.

Not intentional harm —

just an inner structure he hasn’t built yet.

That’s when I remembered:

Kindness doesn’t replace boundaries.

And professionalism requires clarity — not rescue.

06｜This Thanksgiving taught me the exact road I’m meant to walk

The more I see, the more certain I become:

Helping someone build financial structure

isn’t about teaching them to make money.

It’s about helping them build inner order —

the psychological architecture that prevents chaos.

Financial literacy protects families.

Investment education prevents the next tragedy.

And I’m clearer than ever:

Professionalism is responsibility.

Boundaries are compassion.

Clarity is the highest form of kindness.

I’ll continue doing what I do —

with strength, with softness, with presence.

With a deep understanding of human nature

and a commitment to serve without losing myself.

Helping others is my purpose.

Taking care of myself is the boundary that keeps it pure.

And on this Thanksgiving,

I chose to honor both.